Winters parachuted into Normandy in the early hours of D-Day, and fought across France, the Netherlands, Belgium, and eventually Germany. Following the German surrender, he left the 506th and was then stationed in France, where senior officers were needed to oversee the return home. In 1951, during the Korean War, Winters was recalled to the U.S. Army from the inactive list and briefly served as a regimental planning and training officer on staff at Fort Dix, New Jersey. Winters was issued orders for deployment and was preparing to depart for Korea, but instead left the Army under a provision that allowed officers who had served in World War II but had been inactive since to resign their commission.

Winters was discharged from the Army and returned to civilian life, working first in New Jersey and later in Pennsylvania, where he set up his own company selling chocolate byproducts from The Hershey Company to producers of animal feed. He was a regular guest lecturer at the United States Military Academy at West Point until his retirement in 1997. He was the last surviving Easy Company commander.

At Franklin and Marshall Winters was a member of the Upsilon Chapter of Delta Sigma Phi Fraternity and participated in intramural football and basketball. He had to give up wrestling, his favorite sport, and most of his social activities for his studies and the part-time jobs that paid his way through college. He graduated in 1941 with the highest academic standing in the business college. He enlisted in the Army,[5] although he later stated in his memoirs that at the time he "...had no desire to get into the war..." and that he had volunteered so that he would not be drafted at a later date.[4]

Winters enlisted in the Army on 25 August 1941 in order to shorten his time in service.[4] In September, he underwent basic training at Camp Croft, South Carolina.[6] Afterwards he remained at Camp Croft to help train draftees and other volunteers, while the rest of his battalion was deployed to Panama. In April 1942, he was selected to attend Officer Candidate School at Fort Benning, Georgia.[7] It was there he met his friend Lewis Nixon, with whom he served throughout the war in the 101st Airborne Division.[8] He was commissioned as a second lieutenant after graduation from OCS on 2 July 1942.[8]

During the course of his officer training, Winters reached the decision that he wanted to join the parachute infantry.[9] Upon completing training, he returned to Camp Croft to train another class of draftees as there were no positions available in the paratroopers at that time. After five weeks, he received orders to join the 506th Parachute Infantry Regiment (PIR) at Camp Toccoa (formerly Camp Toombs) in Georgia.[10]

He arrived at Toccoa in mid-August 1942 and was assigned to Company E, 2nd Battalion, 506th PIR,[11] later to become better known as "Easy Company" per the contemporaneous Joint Army/Navy Phonetic Alphabet. Serving under First Lieutenant (later Captain) Herbert Sobel, Winters was made platoon leader of 2nd Platoon, earning a promotion to First Lieutenant in October 1942[12][13] and made acting company executive officer,[2] although this was not made official until May 1943.[13] The 506th PIR was an experimental unit, being the first regiment to undertake airborne training as a formed unit.[14] As many of the men had very little previous military experience, the training at Toccoa was necessarily very tough and, as a consequence, there was a high level of personnel attrition. Of the 500 officers who had volunteered, only 148 successfully completed the course. The enlisted men had similar results, with only 1,800 men being selected out of 5,300 volunteers.[14][15]

On 10 June 1943, following further tactical training at Camp Mackall, North Carolina, the 506th PIR was officially attached to the 101st Airborne Division.[16] Later in the year they embarked on the Samaria bound for England, arriving there on 15 September 1943, and disembarking in Liverpool.[17] They then proceeded to Aldbourne, in Wiltshire, where they began an intense training program designed to make the regiment ready for the invasion of Europe that was planned for 1944.[18]

It was while Easy Company was based at Aldbourne that the tension that had been brewing between Winters and Sobel came to a head in November and December 1943.[19] Winters had privately held concerns over Sobel's ability to lead the company in combat for some time before this. Many of the enlisted men in the company had come to respect Winters for his competence and had also developed their own concerns about Sobel's leadership.[20] Winters stated that he never wanted to compete with Sobel for command of Easy Company; however, the situation became out of hand when Sobel attempted to bring Winters up on trumped-up charges for "failure to carry out a lawful order".[21] Feeling that his punishment was unjust and sensing Sobel's tacticality of the matter, Winters requested that the charge be reviewed by court martial. When Winters' punishment was set aside by the battalion commander, Sobel then proceeded to charge Winters with another, separate charge the following day. While the investigation was being undertaken, Winters was transferred to the Headquarters Company and appointed as the Battalion mess officer.[22]

Following this, though Winters tried to talk them out of it, a number of the company's noncommissioned officers (NCOs) gave the regimental commander, Colonel Robert Sink, an ultimatum: either Sobel be replaced, or they would surrender their stripes.[23] Sink was not impressed and several of the NCOs were subsequently demoted and transferred out of the company. Nevertheless, Sink realized that something had to be done and decided Sobel had to be replaced,[24] transferring Sobel out of Easy Company and giving him command of a newly formed parachute training school at Chilton-Foliat.[25] Winters' court martial was set aside and he returned to Easy Company as platoon leader of 1st Platoon. Despite their personality clash, Winters later stated he felt that at least part of Easy Company's success had been due to Sobel's strenuous training and high expectations.[26] In February 1944, First Lieutenant Thomas Meehan III was given command of Easy Company.[25]

Meehan remained in command of the company until the Normandy invasion, when at approximately 1:15 a.m. on 6 June 1944, the C-47 Skytrain transporting the company Headquarters Section was shot down by Germananti-aircraft fire, killing everyone on board.[27] Winters jumped that night and landed safely near Sainte-Mère-Église.[28] After having lost his weapon during the drop, he was able to orient himself, assemble several paratroopers, including members of the 82nd Airborne, and proceed toward the unit's assigned objective near Sainte-Marie-du-Mont.[29] With Lieutenant Meehan's fate unknown, Winters became the de-facto commanding officer of Easy Company, which he remained for the duration of the Normandy campaign.[30]

Later that day, Winters led an attack that destroyed a battery of German 105mm howitzers, which were firing onto the causeways that served as the principal exits from Utah Beach.[31] The Americans estimated that the guns were defended by approximately one platoon of 50 German troops, while Winters had 13 men.[31] This action south of the village of Le Grand-Chemin has been called the Brécourt Manor Assault. Aspects of the attack have been taught at the military academy at West Point as an example of an assault on a fixed position by a numerically-inferior force.[32] In addition to destroying the battery, Winters also obtained a map detailing German gun emplacements in the Utah Beach area.[33]

In September 1944, the 506th PIR took part in Operation Market Garden, an airborne operation in the Netherlands. On 5 October 1944, a German force launched an attack on the 2nd Battalion's flank and threatened to break through the American lines. At the same time, four men in an Easy Company patrol were wounded.[35] Returning to the headquarters, they reported that they had encountered a large group of Germans at a crossroads about 1,300 yards (1,200 m) to the east of the company command post.[36] Realizing the seriousness of the situation, Winters took one squad from 1st Platoon, and moved off toward the crossroads, where they observed a German machine gun firing to the south, toward the battalion headquarters, from an excessive distance.[36] After surveying the position, Winters then led the squad in an assault on the gun crew.[37] Soon after taking the position, the squad took fire from a German position opposite them. Estimating that this position was held by at least a platoon, Winters called for reinforcements from the rest of the 1st Platoon, and led them in a successful assault. Later it was discovered there had been at least 300 Germans.[38]

On 9 October, Winters became the battalion Executive Officer, following the death of the battalion's former XO, Major Oliver Horton.[39] Although this position was normally held by a major, Winters filled it while still a captain. On 16 December 1944, German forces launched a counter-offensive against the Western Allies in Belgium, commencing what has since come to be known as the Battle of the Bulge. The 101st Airborne was trucked to the Bastogne area two days later. Still serving as executive officer of the 2nd Battalion, Winters took part in the defense of the line northeast of Bastogne near the town of Foy.[40] The entire 101st Airborne and elements of the 10th Armored Division battled about 15 German divisions, supported by heavy artillery and armor, for nearly a week before the U.S. Third Army broke through the German lines surrounding Bastogne.[40]

After being relieved, the 2nd Battalion carried out an attack on Foy on 9 January 1945.[41] On 8 March 1945, the 2nd Battalion was move to Haguenau in the Alsace, following which Winters was promoted to major.[42] Shortly afterward Lieutenant Colonel Robert Strayer was elevated to the regimental staff and Winters took over as acting commander of the 2nd Battalion.[43][44]

In April, the battalion carried out defensive duties along the Rhine before deploying to Bavaria later in the month.[45] In early May, the 101st Airborne Division received orders to capture Berchtesgaden.[46] The 2nd Battalion set out from the town of Thalem through streams of surrendering German soldiers and reached the alpine retreat at noon on 5 May 1945.[47] Three days later the war in Europe ended.[48]

After the end of hostilities, Winters remained in Europe as the process of occupation and demobilization began. Even though he had enough points to return to the United States, he was told that he was needed in Germany.[49] Later, he was offered a regular (non-reserve) commission, but declined it.[50] He finally embarked from Marseilles aboard the Wooster Victory on 4 November 1945.[51] He was separated from the Army on 29 November 1945,[51] although he was not officially discharged until 22 January 1946, and he remained on terminal leave until then.[52]

Winters was recommended for the Medal of Honor for his leadership at Brécourt Manor, but received the U.S. Army's second highest award for combat valor, the Distinguished Service Cross, instead.[53] After the release of the Band of Brothers television miniseries, a letter-writing campaign on Winters' behalf began.[32] Rep. Tim Holden (D-PA) introduced HR 3121 (111th) to request the President to grant the Medal, but the bill was referred to the House Armed Services Committee Subcommittee on Military Personnel, dying in committee in 2007.[54]

Following the end of the war in the European theater, Winters worked for his close wartime friend Captain Lewis Nixon at Nixon's family business, Nixon Nitration Works of Edison, New Jersey, rising to become general manager in 1950.[55] On 16 May 1948, Winters married Ethel Estoppey[2][56] and continued to pursue his education through the GI Bill, attending a number of business and personnel management courses at Rutgers University.[56]

In June 1951, Winters was recalled to active duty in the Army during the Korean War.[56] He was ordered to join the 11th Airborne Division at Fort Campbell, Kentucky, but he was given six months to report and in this time he traveled to Washington, D.C. to speak to General Anthony McAuliffe, in the hope that he could convince the Army not to send him to Korea.[56] He explained to McAuliffe that he had seen enough of war and apparently McAuliffe understood his position, but explained that he was needed because of his command experience. Winters then reported to Fort Dix, New Jersey, where he was assigned as a regimental planning and training officer.[57]

While at Fort Dix, Winters became disillusioned with his job, finding that he had little enthusiasm for training officers who lacked discipline and did not attend their scheduled classes. As a result, he volunteered to attend Ranger School.[57] He then received orders to deploy to Korea and traveled to Seattle, where, during pre-deployment administration, he was offered the option of resigning his commission,[57] which he accepted.

He was discharged from the Army and became a production supervisor at a plastics adhesive business in New Brunswick, New Jersey.[57] In 1951, he and his wife bought a small farm where later they built a home and raised two children. In 1972, he went into business for himself, starting his own company and selling animal feed products to farmers throughout Pennsylvania.[57] Soon afterward, he moved his family to Hershey, Pennsylvania.[2] He finally retired in 1997.[58]

During the 1990s, Winters was featured in a number of books and television series about his experiences and those of the men in Easy Company. In 1992, Stephen Ambrose wrote the book Band of Brothers: Easy Company, 506th Regiment, 101st Airborne from Normandy to Hitler's Eagle's Nest, which was subsequently turned into an HBOmini-seriesBand of Brothers.[2][59] Winters was also the subject of the 2005 book Biggest Brother: The Life of Major Dick Winters, The Man Who Led the Band of Brothers, written by Larry Alexander. His own memoir, Beyond Band of Brothers: The War Memoirs of Major Dick Winters, co-written by military historian and retired U.S. Army Colonel Cole C. Kingseed, was published in early 2006.[2][60] He also gave a number of lectures on leadership to cadets at the United States Military Academy at West Point.[59]

On 16 May 2009, Franklin and Marshall College conferred an Honorary Doctorate in Humane Letters upon Winters.[61]

Despite the many accolades he had received, Winters remained humble about his service.[62] During the interview segment of the miniseries Band of Brothers, Winters quoted a passage from a letter he received from Sergeant Mike Ranney, "I cherish the memories of a question my grandson asked me the other day when he said, 'Grandpa, were you a hero in the war?' Grandpa said 'No...but I served in a company of heroes'."

Winters was buried in the Bergstrasse Evangelical Lutheran Church cemetery in Ephrata, Pennsylvania, in a private ceremony.[65] He is buried next to his parents in the Winters' family plot. His grave is marked "Richard D. Winters, World War II 101st Airborne". His wife Ethel died in 2012, at age 90.